


Alexa, Play Careless Whisper

by Iblis_Daughter



Category: Supernatural
Genre: Alternate Universe - Human, Alternate Universe - It's a Terrible Life (Supernatural), Alternate Universe - Modern Setting, Alternate Universe - Office, Bottoming from the Top, Chair Sex, M/M, Plot What Plot/Porn Without Plot, Size Difference, Size Kink, Top Castiel/Bottom Sam Winchester, Topping from the Bottom, abuse of an office chair, improper usage of office supplies, stupid tags but didn't want to make the fic unfoundable
Language: English
Status: Completed
Published: 2019-04-25
Updated: 2019-04-25
Packaged: 2020-01-31 06:18:10
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,172
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18585502
Author URL: https://archiveofourown.org/users/Iblis_Daughter/pseuds/Iblis_Daughter
Summary: It wasn't enough that Castiel Milton had somehow lost the Excel spreadsheets to the Sandover-Roman deal when his computer decided to break down.Now, he had to callthatIT man from downstairs for help, the one with the ridiculous, stupid, shiny hair and insistence on being goddamntallall the time.





	Alexa, Play Careless Whisper

**Author's Note:**

> Shameless PWP involving:
> 
> \- chair riding  
> \- a lot of sexual frustration  
> \- an awful title
> 
> I needed a small break from completing the ending of _a cathedral to your name_ , but rest assured it's getting finished.

It was the end of everything.  
  
There had been a mysterious beeping noise in his cubicle that he couldn't find the source of for weeks _,_  his mouse had begun moving on its own and keyboard begun typing in various obscure porn sites, and it turned out to be Dean Smith in the next cubicle, who had nearly fallen over with red-faced, wheezing laughter at the sight of his frustration.  
  
Castiel thought that maybe that was when it had began, the end. The incessant beeping had driven him up the wall and still was nowhere to be found, so he had gotten the phone(thankfully not in jello this time)and asked Charlie to send up IT while ignoring Dean snapping rubber bands at his head from a tiny clothespin gun and his impending migraine.  
  
"He'll be right up," Charlie promised from the other end of the line. Then, quietly sympathetic, "Do you want me to put laxatives in Dean's salad for you, Cas?"   
  
   "No, I'll be alright, I'm used to it; if you do that it will only encourage him," he answered, pinching the bridge of his nose as his frontal lobe began to throb. How Smith managed to get anything done with all his screwing around, he didn't know.  
  
"You can just use Alexa next time to call me, y'know," Charlie added before hanging up, leaving Castiel to glare distrustfully at the new piece of technology Mr. Adler had decided to add to the office. A gentle knock- to the side of his cubicle wall had startled him out of his thoughts.  
  
"Mr. Milton?"   
  
And it was about this point where everything had slid downhill. Castiel blinked at a pair of khaki legs standing in his entrance and slid up their impossible length to the eyes of their owner. The IT man smiled widely with a lot of teeth( _too many_ , Castiel thought).  
  
"You called? I'm Sam Wesson," he said pleasantly, throwing out a hand. Castiel stared blankly at it for a few seconds before tentatively shaking it, and Sam shook with an iron enthusiastic grip that nearly dislocated his shoulder.  "What did you need assistance with?"  
  
"Um, yes," he found his voice finally, and cleared his throat. Sam smiled patiently. "There is a very annoying beeping sound somewhere inside my cubicle, and I have been unable to locate it for several weeks. And," he hesitated, "There is something else."  
  
Sam cocked his head, listening, and sure enough, there was a cheery  _beep._  Castiel could feel his jaw tic.  
  
"It's been weeks," he said tensely. "I took apart my des-"  
  
Sam reached over his head with impossibly long arms, and the words became strangled somewhere in Castiel's throat. The IT guy plucked something the size of a button off the other side of the wall("Hey," Dean protested) and flicked it into his awful yellow shirt pocket. He grinned victoriously.   
  
"You couldn't see it cus you're a bit, uh." The grin grew wider, his arms seemingly not in any hurry to remove themselves from where they were caging him in, and Castiel decided he also hated them. "Short."  
  
"I'm a perfectly average height," Castiel retorted, crossing his arms. "Taller, actually."  
  
Sam shrugged, his auburn hair bouncing on his broad shoulders. "Everyone's short to me."  
  
Castiel scowled. "Is that regulation?" he asked instead, jabbing a finger at the dumb-looking, overly shiny hair.  
  
Sam shrugged again, and Castiel contemplated whacking the man out of his personal space with a stapler on one of his impossible shoulders. He now knew why Gabriel had tried so many times to give him the social skills talk. It was downright uncomfortable on the other end.  
  
His eyes roved over him almost appreciatively, lingering, and he suppressed a shiver, settling for crossing his arms tighter and glaring.  
  
"I mean, you're kind of rumpled, really think you should be talking about that?" Sam chuckled.   
  
   "My eyes are up here, Mr. Wesson," Castiel snapped. Sam straightened, but took his time sliding his arms back to his sides.   
  
"That they are," Sam said, grinning his stupid placating smile and scratching at his stupid long hair. He didn't break eye contact. "Well. Down there, if you wanna be technical."  
  
Castiel stalked over to his desk. "There's something else. With my mouse and keyboard."  
  
Sam quirked an eyebrow at the various tabs of porn. "What, this isn't just you on company time?"  
  
"No," Castiel snapped again. He did his best to valiantly ignore the canned moan coming from a side ad. The other eyebrow was raised in the most annoying habit he had ever seen.   
  
He fidgeted and flushed.  
  
Sam reached under the desk and pulled out a tiny USB. He tossed it over the wall into Dean's cubicle("Not cool, man!").   
  
"You ever thought about just asking him to stop?" Sam tapped his fingers on the keyboard, closing down the tabs.   
  
   "Acknowledgement is encouragement," Castiel sighed. Sam hovered over a tab of gay BDSM before shutting it down.  
  
"Is it, now?"   
  
   "Thank you for your assistance, Mr. Wesson," Castiel said curtly. "That will be all for now. Good afternoon."  
  
"Oh, you'll need me back?"   
  
   "I said, good afternoon, Mr. Wesson!" Castiel said louder than he meant to, and cursed inwardly at the top of Dean's head popping over the wall in curiosity. Sam nodded pleasantly and sashayed horribly and awfully away down the hall.   
  
"That's the highest I've ever heard your voice, man." Dean smirked, still in no hurry to move from where he was perched on top of his chair's back overlooking the wall, and slowly span in place. "What, the nerdy Green Giant touch you in the no-no square while reciting Latin backwards?"  
  
   "Go back to work, Smith."  
  
Dean leaned forward, threatening to tip over the wall. "Gigantor Bill Gates tickle your pickle? Pick you up and jiggle you like a fleshlight snowglobe? Legolas'd your Gim- _ow!_ "  
  
Castiel wouldn't admit it, but there was a small nugget of satisfaction in his gut at Dean's surprised yelp when he took the stapler and lobbed it at the direction of his skull. There was comically frantic flailing as he tried to balance on the chair, and then a equally satisfying thump on the cheap office carpet.  
  
                                                                      *    *    *  
   
The second part of the apocalypse struck less than a week later.  
  
The financial details of the Sandover-Roman deal had been dropped in Castiel's lap to input into the system. There was probably something to be said about the irony of a corporation purchasing an Alexa and having their employees enter numbers into an Excel spreadsheet, but Castiel couldn't focus on that right now.  
  
He stared blankly at the screen. It greeted him with darkness.  _All that work,_ he thought bitterly.  _The past four hours. Gone._  
  
"I'm sorry, Cas," Dean said from over his shoulder. He bumped his arm affectionately with his Styrofoam cup. "You're a busy bee, you'll get it all back up soon."  
  
"It would've been easier if you hadn't messed with it so much," Castiel muttered. Dean rolled his eyes.  
  
   "It's fine, I'll go call your BFG," Dean said. "Hey, Alexa? Call Charlie."  
  
"Dean." Castiel hated the slight edge of a whine that crept into his voice. "Please. I can just use another computer or sort it out on paper. It'll take longer, but I'll be fine."  
  
   "You sure?"  
  
"Positive. Thank you."  
  
Dean spun around in his chair idly. "Terminator really did a number on you, huh?"  
  
He slammed open the dusty netbook laptop harder than he meant to. "No. And am I to assume you know him, judging from all these nicknames?"  
  
Dean shot him a shit-eating grin. "He's my brother from another father. Different dads, different last names, same weird freckle on our asses. He started here three weeks ago."  
  
"Wonderful," Castiel said bitterly, "Two of you."  
  
And he got to work.  
  
Work, it turned out, lasted far into the afternoon. He skipped lunch. Without his usual computer, everything was painfully slow, and the netbook's return key refused to cooperate. It also rejected every mouse he tried to plug into it, leaving Castiel to stubbornly drag his finger across the trackpad every time he needed to enter another bit of data. It was tedious.  
  
It was five when Dean came over to him and leaned on his desk. "You coming with us to the bar, Cas?"  
  
Castiel barely looked up, and he frowned at the screen in concentration. The little white boxes of the ancient spreadsheet were starting to blur together. He blinked up at Dean.  
  
"Hm?"  
  
   "The bar," Dean repeated patiently. "Everyone's going home soon or left already. You coming? Gabe said he'll buy you a vodka milkshake with all the sad Skittles you want if you promise not to cry-lecture the bartender on the mating habits of deep sea fish again."  
  
"Gabriel  _is_ the bartender, and he asked about them," Castiel retorted. "And...no. I need to finish up here. Mr. Adler already knows I'm alright for overtime."  
  
Dean tapped the desk and thumped him on the back. "Suit yourself. Have fun and lock up or Adler'll have your hide."  
  
He was left alone to stare at an unforgiving screen. Castiel gave it another half-hearted go for forty more minutes, the sun outside slowly creeping towards evening. Finally, he gave up and slapped the laptop shut. He rubbed his eyes. At least this way there was time for the bar, and he could worry about the forms on Monday. Yes. A lot of liquor, whatever Gabriel had in the bar kitchen, and then bed.   
  
A gentle knock startled him out of his reverie. Castiel jumped in place, fumbling with the netbook as he almost dropped it. Sam Wesson was eclipsing his entryway and grinning away. His ridiculous hair was tied back loosely, and it framed his cheekbones perfectly.  
  
Castiel glared.   
  
"Thought you would've gone home by now," Sam said in lieu of a proper greeting.   
  
    "Some of us work, Wesson," Castiel scowled. Sam strode over to loom over his head while leaning cross-armed against the desk. It was a very Dean-like habit, and Castiel could see the resemblance. It was a bit jarring, and he didn't appreciate it.   
  
"Stop," he started as Sam bent over his shoulder to fiddle with the computer cords, "Wesson, what are you doing-"  
  
The screen flickered to life, and Castiel gaped. Sam patted his stiff shoulder without moving from his position, and Castiel could feel the irritating grin next to his cheek.  
  
"Dean must've unplugged your monitor and gotten that USB back in," he said, and Castiel did not like how close to his ear his voice was. "But on the other hand, it looks like he did it all for you already, and the forms for Monday."  
  
Sam began making lazy circles with his frankly massive hands on his shoulderblades.  
  
"Wesson." Castiel found his voice again. "I repeat. What. Are you doing."  
  
   "You seemed tense," Sam said innocently. And was that a  _blush_? Sam cleared his throat. "And, well...my brother talks about you all the time, but now that I've actually met you? You're kind of cute."  
  
"I beg your pardon," Castiel spluttered. "I am a grown man."  
  
   "Yes, you are," Sam purred, and Castiel let out an unmanly squeak as his lap was suddenly filled with gigantic IT technician. Sam's Chrysler building long legs were astride his hips, arms casually thrown behind his neck. From here, if he craned his neck upwards, he could count Sam's eyelashes.  
  
Castiel made a noise like a dying teakettle.  
  
"Why are you so tall?" he demanded. "And forward. What gives you the right?"  
  
Sam shrugged. "Dean said you were a little oblivious to flirting, so I figured this was the best approach. If you want me off, though, I can go. Though I kind of like you all flustered even more."  
  
   "Well, you're already here," Castiel snapped. He could feel the heat rising to his cheeks as Sam quirked a brow and a lip and started massaging his collarbone.   
  
"Tsk, tsk, Mr. Milton," Sam breathed against the hollow of his throat, and Castiel thought he might actually stick his head in the printer and die, "So tense. Why don't you let me take care of that?"  
  
   "Shut the _hell_  up and stop asking stupid questions," Castiel hissed, and before he could think better of it, he had tangled fingers in that ridiculous, stupid ponytail and tugged his face into his own.   
  
It was heated and messy, and Castiel channeled his week's frustrations into it through his teeth. And,  _Christ,_ even Sam's tongue was big, flicking leisurely at his mouth and sweeping big firm laps onto his own. Sam's massive hands were planted on his cheeks, thumbs stroking his jaw through the stubble. It sent a livewire straight to his groin, and he shifted unconsciously upwards to claw at Sam's back and fumble out a groan. His hips wanted to move but Sam's weight kept them pinned.  
  
Sam bit at the juncture between his neck and shoulder through his purple waistcoat, and he lifted up so Castiel's hips stuttered awkwardly into the air. From this position, he was still essentially standing, and the thought made Castiel's mouth dry and his head dizzy.  
  
"Cas, you're so hot like this," Sam breathed into his ear, and he shuddered. "Ever since I saw you weeks ago at that shitty donut station downstairs, with your boring coat folded over your arm, ass tight in those slacks, I knew I wanted you. Dean is missing out."  
  
   "I would prefer if you did not talk about your brother during this," Castiel gasped at the sudden loss of bodyweight as Sam slid down to rest two hands on his thighs, fingers deftly working at his zipper, "And it's creepy you have been watching me in this manner for weeks. We had an entire sexual harassment seminar- _oh, God..._ "  
  
His words were cut off in a strangled noise when Sam casually shoved his entire dick in his mouth to the root, looking up at him through his ludicrous curtain of mussed hair as his hands rubbed circles into his knees. He pulled agonisingly slowly off with a pop, tongue dipping into the slit and around the head. Castiel let out a frustrated moan.  
  
"I'm sorry, were you talking?" he said sweetly.   
  
   "Nnngh," Castiel replied.  
  
"I'm sorry, Cas, that's not a programming language I've learned yet," Sam said apologetically. His tongue flattened over the head as he sucked languidly up and down his length. "Though they say once you learn one, you kinda figure out the rest. And I know how to make your software into hardware."  
  
   "Shut. Up," Castiel gritted out from behind his teeth, hands over his eyes. Sam chuckled, low and playful, fingers tugging at the edge of his shirt to slip under to tease the heaving flesh of his stomach while dragging his pants lower. Castiel heard another zipper being undone, and he peeked out from under his fingers to see Sam holding a small bottle of lube in his grinning teeth as he wiggled out of his own pants. He settled himself back onto Castiel's lap, the heat of his bare legs caging him in and their crotches slotting together deliciously. Sam leaned to rest his forehead against his.  
  
"Hey, Cas."  
  
   "...Wesson," Castiel replied gruffly. He knew he must be quite a sight, flushed pink and hair like he had stuck a finger into the faulty socket behind the copier again.  
  
"How about you be the USB and I'll be the port?"  
  
 Sam's hand gripped his shoulder for balance as the other dipped behind him.  
   
   "Oh, Christ," and Castiel didn't mean for it to sound so much like a whimper. Sam's cock bounced freely and slapped against his stomach, huge and thick and leaking steadily against the hitched up fabric. Castiel gave it a few experimental tugs, and Sam hummed appreciatively.  
  
"Next time you can get into the maintenance closet and you can handle my exception," Sam whispered against his earlobe. Castiel shivered and squirmed.   
  
"For the love of all things holy,  _please_ shut up."  
  
   "No, you," Sam said maturely, and reached behind him to pick up the tape. He smiled widely as he slapped a wide swath over Castiel's mouth, leaving his lips exposed, then mouthed wetly at them. He let out a muffled moan, reaching up, and Sam caught both his wrists in one hand while the other diligently worked fingers in and out of himself, hips hovering obscene figure-eights over his neglected cock.   
  
Then, the great expanse of Sam was impossibly closer, and slid all at once onto his dick in pulsing, tight heat.  
  
Castiel screamed through the makeshift gag. He could cry. He could compose poetry about Sam's fucking  _perfect_ ass setting a ruthless pace bouncing up and down his cock, of the great mountain of a man panting as he rode Castiel into mindless oblivion on his abused, creaking office chair, of the slick drag of his ass as he flexed his great legs up until it nearly edged off his rim and  _slammed_ down with the force of a Soviet powerlifter, grunting with barely any exertion as his thighs slapped against his own.   
  
He felt bad for the janitor who would have to clean up his melted brains off the carpet in the morning.  
  
"God, yeah, Cas, so good, your cock is so good in me, filling me up like that, look at you, fuckin' destroyed..."  
  
   "Mmph!" Castiel sobbed in helpless pleasure, hips jerking in place, and his eyes rolled into his head as he came so hard he saw his life flash before his eyes. Sam groaned, loud and deep, before following soon after.   
  
He rested his head on Castiel's, panting. His softening cock was still inside him, and Sam didn't seem to be in any hurry to move. Instead, he took off the tape. Castiel winced. He felt boneless, somehow, like he was floating somewhere in space instead of in his office cubicle.  
  
"You're going to take off Monday," Sam said brightly, and he was already up and about now, pulling back on his khaki slacks and zipping Castiel back up. He offered a hand to him to help him up, and Castiel accepted. He stood on unsteady, shaky legs and nearly fell over before Sam caught him, chuckling.  
  
   "You are a demon, Mr. Wesson," Castiel muttered darkly. The waistcoat was most likely ruined but he had a trenchcoat somewhere. It felt like a piece of his soul had been sucked out and replaced with dehydration.  
  
"Maybe," Sam said cheerfully, "Let's go get your car. We can make it to the bar, and afterwards, you can show me your place. I think your stress is worse than I thought, it's going to take all weekend to work out all the kinks."   
  
Castiel huffed and glared but as they were in the elevator going down to the basement level, he couldn't help but steal glances at Sam's beaming face in the reflection of the buttons.  
  
Maybe the apocalypse wasn't so bad after all.  
  
                                                                         *   *   *  
  
  
  
  
  


**Author's Note:**

> Not a kudos/comments whore but appreciate them all the same, and when I have enough I will print them out and stack them up and create the world's most beautiful paper mache dildo.


End file.
